Dealkenylative Alkynylation Using Catalytic FeII and Vitamin C,Journal of the American Chemical Society

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Dealkenylative Alkynylation Using Catalytic FeII and Vitamin C
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2022-08-04 , DOI: 10.1021/jacs.2c05980
Manisha Swain ₁ , Thomas B Bunnell ₁ , Jacob Kim ₁ , Ohyun Kwon ₁

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In this paper, we report the synthesis of alkyl-tethered alkynes through ozone-mediated and Fe^II-catalyzed dealkenylative alkynylation of unactivated alkenes in the presence of alkynyl sulfones. This one-pot reaction, which employs a combination of a catalytic Fe^II salt and l-ascorbic acid, proceeds under mild conditions with good efficiency, high stereoselectivity, and broad functional group compatibility. In contrast to our previous Fe^II-mediated reductive fragmentation of α-methoxyhydroperoxides, the Fe^II-catalyzed process was devised through a thorough kinetic analysis of the multiple competing radical (redox) pathways. We highlight the potential of this dealkenylative alkynylation through multiple post-synthetic transformations and late-stage diversifications of complex molecules, including natural products and pharmaceuticals.

中文翻译：

使用催化 FeII 和维生素 C 进行脱烯基烷基化

在本文中，我们报道了在炔基砜存在下，通过臭氧介导和 Fe ^II催化的未活化烯烃的脱烯基炔基化合成烷基链炔烃。这种一锅反应采用催化 Fe ^II盐和L-抗坏血酸的组合，在温和的条件下进行，具有良好的效率、高立体选择性和广泛的官能团兼容性。与我们之前的 Fe ^II介导的 α-甲氧基氢过氧化物还原断裂相比，Fe ^II催化的过程是通过对多个竞争自由基（氧化还原）途径进行彻底的动力学分析而设计的。我们强调了这种脱烯基炔基化通过复杂分子（包括天然产物和药物）的多次合成后转化和后期多样化的潜力。

更新日期：2022-08-04

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